Boston, MA


Browse by SailingBoston Sailing is a well known local and tourist activity and is the perfect way to do some Harbor sightseeing by boat.  Join us with our professional crew and take to the waters to sail Boston Harbor aboard Schooner Adirondack III. Let our amazing crew dazzle you with their sailing skills and top-notch customer service. Boston sailing is fun, but sailing and sightseeing is the most wonderful way to experience Beantown. Sail past Boston’s Waterfront to see the U.S.S. Constitution, Fort Independence (named by George Washington), Marriott Custom House Tower, U.S.S Cassin Young, and see the steeple of the Old North Church in Boston’s North End. This city skyline and local Islands are a must see when visiting (or just needing a escape from the city) and you can enjoy all of these sites with a glass of wine or Champagne in hand aboard our 80-foot schooner, Adirondack III.  We not only offer the most premium sailing experience in Boston, but have 5 star reviews for our service.  

Boston Day Sail

Within minutes of leaving the dock, you’ll forget the distractions of life on land, as you experience the joy of a leisurely sailing cruise. Our classic afternoon day sails are the perfect way to see the sights of Boston Harbor. There is no better way to enjoy the day than sailing aboard the schooner Adirondack III, which is the most elegant sailing excursion you will find in the harbor. Adirondack III is a classically styled 80-foot pilot schooner with long sleek lines. She is smooth and gentle sailing vessel with some speed.

  Duration: 2 hrs   Boat: Adirondack III   Cost: $45

Boston Sunset Sail

Experience a beautiful Boston Harbor sunset on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. Sailing offers a smooth and gentle experience on the water, which is great for having a romantic early evening out with that special someone. Our crew and captain offer top notch customer service to our guests.

  Duration: 2 hrs   Boat: Adirondack III   Cost: $55 - $57

Boston City Lights Sail

For the ultra-romantic choose our City Lights Sail aboard our sailboat. This serene sail allows you to experience Boston with peaceful tranquility. Enjoy the evening sea breeze swirling around you and all of Boston’s twinkling lights as your backdrop. Take-in the shimmering city of Boston on a smooth and gentle sail. Blankets are available to guest upon request on chilly nights. Cozy up with a loved one on the decks of our beautiful schooner.

  Duration: 1.5 hrs   Boat: Adirondack III   Cost: $40

Boston USS Constitution Turnaround Sail

USS Constitution Turnaround Sail

Once a year the USS Constitution heads out of the harbor to Fort Independence for a 21-gun salute. Sail along side our oldest operating warship used to train sailors in the US Navy as she cruises through Boston Harbor. Folks line the shoreline to watch the Constitution on one of her rare trips, get front row seats on the schooner Adirondack III as we escort our brave ship down to Fort Independence. (Unfortunately, the USS Constitution is at dry dock until 2018. Check back for tickets to watch the Turnaround Sail in spring of 2018.)

  Duration: 2 hrs   Boat: Adirondack III   Cost: $125

Winthrope Fireworks Cruise with Classic Harbor Line

Winthrop 4th of July Fireworks Cruise and Sail on Adirondack III

Don’t want to deal with all the traffic crowds and hype surrounding the 4th of July, but still want to celebrate and enjoy the patriotic holiday? Step aboard the Adirondack III for a cruise to Winthrop to watch the fireworks and then sail back to Boston at the end. Sip on Champagne and enjoy this magical evening with the best seats in the house! 

  Duration: 3 hrs   Boat: Adirondack III   Cost: 75.00

Labor Day Fireworks Cruise Aboard Adirondack III

What better way to celebrate the end of summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard beautiful Adirondack III for a magnificent Labor Day cruise. This 1.5-hour cruise offers guests the opportunity to soak up Boston’s colorful fireworks display from an awesome vantage point, practically right underneath them and out on the water! (The event does not sail and offers spectacular views of the fireworks)

  Duration: 2 hrs   Boat: Adirondack III   Cost: $75